Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes

被引：65

作者：

Jinks, Michael A. ^{[1
]}

de Juan, Alberto ^{[1
]}

Denis, Mathieu ^{[1
]}

Fletcher, Catherine J. ^{[1
]}

Galli, Marzia ^{[1
]}

Jamieson, Ellen M. G. ^{[1
]}

Modicom, Florian ^{[1
]}

Zhang, Zhihui ^{[1
]}

Goldup, Stephen M. ^{[1
]}

机构：

[1] Univ Southampton, Chem, Southampton SO17 1BJ, Hants, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 45期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

chirality; CuAAC; rotaxane; stereoselective synthesis; supramolecular chemistry; AZIDE-ALKYNE CYCLOADDITION; ACTIVE-TEMPLATE SYNTHESIS; EFFICIENT DIAZO-TRANSFER; INTERLOCKED MOLECULES; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYSIS; ALPHA-CYCLODEXTRIN; SOLOMON LINK; CATENANES; MACROCYCLES;

D O I：

10.1002/anie.201808990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available alpha-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.

引用

页码：14806 / 14810

页数：5

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